Stereoselective nucleophilic substitution of 6-(tert-butyldimethylsilyloxy)-3,6-dihydro-2H-pyran-3-yl acetate: application to the synthesis of a NK1 receptor antagonist

Tetrahedron Letters

Volumn 48, Issue 21, 2007, Pages 3723-3726

  Sugawara, Kazutoshi ^a   Hashiyama, Tomiki ^a  

^a MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ACETYLENE DERIVATIVE; BENZYL ALCOHOL; CARBAMIC ACID DERIVATIVE; LEWIS ACID; NEUROKININ 1 RECEPTOR ANTAGONIST; PYRAN DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; CIS TRANS ISOMERISM; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 34247184099     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.104     Document Type: Article

References (12)

1. Sugawara K., Imanishi Y., and Hashiyama T. Tetrahedron: Asymmetry 11 (2000) 4529
2. Aggarwal V.K., and Vennall G.P. Tetrahedron Lett. 37 (1996) 3745
3. Synthesis of 7a and 7b from Pentose glycals see:. Hosokawa S., Kirschbaum B., and Isobe M. Tetrahedron Lett. 39 (1998) 1917 and reference cited therein
4. Chamberland S., Ziller J.W., and Woerpel K.A. J. Am. Chem. Soc. 127 (2005) 5322 and reference cited therein
5. Synthesis of the enantiomers of 8b from 3,4-di-O-acetyl-d-xylal, see:. Cristina F., Roberta G., Giovanna M., and Matio O.T. Tetrahedron: Asymmetry 12 (2001) 2731 and reference cited therein
6. 3 medium after allowing to stand at room temperature for 1 week.
7. Nelson T.D., Rosen J.D., Smitrovich J.H., Payack J., Craig B., Matty L., Huffman M.A., and McNamara J. Org. Lett. 7 (2005) 55 and reference cited therein
8. Owen, S. N.; Seward, E. M.; Swain, C. J.; Williams, B. J. U.S. Patent 6,458,830 B1, 2001.
9. Brands K.M.J., Payack J.F., Rosen J.D., Nelson T.D., Candelario A., Huffman M.A., Zhao M., Li J., Craig B., Song Z., Tschaen D.M., Hansen K., Devine P.N., Pye P.J., Rossen K., Dormer P., Reamer R.A., Welch C.J., Mathre D., Tsou N.N., McNamara J.M., and Reider P.J. J. Am. Chem. Soc. 125 (2003) 2129
10. Frigerio M., and Santagostino M. Tetrahedron Lett. 35 (1994) 8019
11. Kobayashi S. Chem. Lett. 12 (1991) 2187
12. All new compounds were fully characterized.